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Synthesis 1989; 1989(4): 337-340
DOI: 10.1055/s-1989-27249
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Pyrrole aus 3-Alkoxyacroleinen und CH-aciden α-Aminoessigsäure-Derivaten

Gul Hassan Walizei* , Eberhard Breitmaier
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-5300 Bonn 1, Federal Republic of Germany
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Publication Date:
17 September 2002 (online)

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Pyrroles from 3-Alkoxyacroleins and CH-acidic α-Aminoacetic Acid Derivatives 2-Alkoxycarbonylpyrroles and 2-cyanopyrroles 4 are prepared in a one-step synthesis by vinylogous amidation of 3-alkoxyacroleins 1 with glycine ester 2a-c and aminoacetonitrile (2d), followed by basecatalyzed cyclodehydration of the intermediate 3-aminoacroleins 3. The 3-hydroxypropyl function can be introduced into the pyrrole ring by using 3,4-dihyrdo-2H-pyran-5-carbaldehyde (5) as a cyclic 3-alkoxyacrolein.

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